


Little Black Book

by sinfuldesire_archivist



Category: Supernatural
Genre: During Canon, First Time, Humor
Language: English
Status: Completed
Published: 2007-07-09
Updated: 2007-07-09
Packaged: 2018-09-03 14:13:13
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,237
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8716978
Author URL: https://archiveofourown.org/users/sinfuldesire_archivist/pseuds/sinfuldesire_archivist
Summary: Desperate to tell Dean how he feels about him, Sam consults 3 unlikely experts from Dean's little black book.





	

**Author's Note:**

> Note from the Sinful Desire archivists: this story was originally archived at [Sinful-Desire.org](http://fanlore.org/wiki/Sinful_Desire). To preserve the archive, we began importing its works to the AO3 as an Open Doors-approved project in November 2016. We e-mailed all creators about the move and posted announcements, but may not have reached everyone. If you are (or know) this creator, please contact us using the e-mail address on [Sinful Desire collection profile](http://archiveofourown.org/collections/sinfuldesire/profile).

  
Author's notes: Hope you enjoy. Sex only occurs between Sam/Dean but sex between Dean and other characters is strongly implied, and by implied I mean explicitly stated. Dedicated to all those who have slept with, or have dreamt of, sleeping with Dean Winchester. Keep on reaching for that rainbow.  


* * *

 

“Fuck!” Dean yelled, massaging his cock with one hand, using the other to turn up the volume on the television.  
  
_"Debbie Does Dallas"_ was playing on the television, much to Sam’s dismay.  
  
“Never let Dean pick the porn,” he said to himself, grasping his own cock and pushing himself slowly towards orgasm.  
  
“I heard that Sam,” Dean said with a groan, fisting his cock a little faster with his little brother right next to him.   
  
“This is a classic!” Dean exclaimed. “Didn’t they teach you anything at that stuck up school?”  
  
“I didn’t take porn 101.”   
  
Dean grasped himself tightly, stroking his length and pushing his jeans and boxers down lower past his knees as he prepared for the inevitable.   
  
Sam’s eyes couldn’t help but stray from the television to Dean’s cock every now and again. Taking glances long enough to satisfy himself, but short enough so Dean wouldn’t notice.  
  
“You sure this isn’t a _little_ weird Sammy?” Dean said with a groan, continuing to fist himself.  
  
“The guys in college do it all the time,” Sam replied rather cheekily.   
  
“Right.” Dean replied, trying to pretend this wasn’t the least bit unusual.  
  
Dean came first, his cock erupting with his thick come, filling his fist and shooting all the way onto the table in front of him with a loud groan.  
  
Sam looked on intently, the sound of Dean coming sent him spiraling over the edge, making him lose all control. The thick mess had coated his hands but the feeling was too intense for him to care.  
  
Sam stared at Dean, who was apparently recovering from his orgasm, his face sweaty and his breath labored. There was something about his brother he just couldn’t figure out.   
  
What made him horny? What made him tick? What made him groan, moan and come? He was determined to find out.  
  
*****X*****  
  
“I’m gonna take a shower!” Dean yelled as Sam began his work. It was in there somewhere. He pushed and tossed the clothes in Dean’s duffle aside. Underneath a pair of black boxers and several layers of plaid jackets he finally found it. Dean’s _little black book_. Every person Dean had ever slept with, fooled around with, or simply fucked was listed, in alphabetical order no less.  
  
The thing was huge, I’m talking biblical.   
  
“Wow, that’s a lot of names,” Sam said to himself thumbing through the pages. “Angie Graham, Beth Ryder, Christine Daliday, Evan Lara, and that bitch Suzie Syzmanski, to name a few.”  
  
He checked book, finding a few names that were in the area.   
  
Dean came out of the shower with a towel wrapped around his waist, dripping wet.   
  
“What ya doin’ Sammy?” He asked seeing his empty duffle and clothes thrown askew.   
  
“Um, condoms, yeah, I need condoms. I – er, I ran out.”  
  
“No problem,” Dean said handing him a handful from the zipper pocket.   
  
“Now don’t go using them all in one place,” he teased. “I’m seriously tired of this motel,” Dean continued. “I wanna go out, wanna come with?”  
  
“No thanks. I’m cool here,” Sam mumbled finding the perfect opportunity to set his plan in motion.  
  
*****X*****  
  
Sam called each person, scheduling them to meet him at the motel he was staying at. He was nervous as hell. Understandably after most of the people he called Dean had slept with and then skipped town the next day.   
  
The hard part was getting them to actually meet with him. Dean got around all right. Sam just didn’t know how bad it was until he made the first few calls. The first 5 people he called hung up the phone as soon as he said, “Dean.”   
  
Sam chuckled at the thought of what he as about to do. Did he really want to go through with this? Wacky things seemed to come naturally to the Winchester brothers, but this, _this_ was on a whole different level.  
  
A knock on the door interrupted his thought. “Too late to turn back now,” he said to himself.   
  
*****X*****  
  
“Hello darling,” the tall blonde woman said as she entered the motel room, her purse in one hand and her compact in the other.  
  
Heather Stevens was her name, the first girl Dean ever slept with. “You know Sammy, I was rather annoyed when you mentioned Dean, but when I found out you wanted to see me, I must admit, I got a little excited.”  
  
“When you walked in on us that night, I though you would be too embarrassed to talk to me again,” she continued.  
  
“It’s Sam,” he replied, “and I didn’t call you for that. I need to talk with you – about Dean.”  
  
Sam remembered that night when he walked in on Dean and Heather. Heather was one of the hottest girls in their neighborhood and leave it to Dean to be the first one to fuck her. Dean yelled at him for weeks about always knocking before coming into his room again, but being a little brother he of course ignored it every time. He also couldn’t shake the memory of how he couldn’t take his eyes off of Dean’s smooth, sweaty, muscular body and how he forgot all about Heather. That was in the past however and things had since changed.  
  
Granted, he wasn’t too hot about taking up Heather on her offer for sex now either. Her looks had faded, alcoholism hit her hard. She had been divorced 3 times already and hit the bottle a little harder after each one. She didn’t look like she had gotten much sleep in a long time. Her once rosy cheeks were now pale with caked on foundation, and her long lashes were now a little less than inviting.  
  
“So you had sex with Dean, right?” He said shyly.  
  
“You should know Sammy, you walked in on it 2 times.”  
  
“It’s Sam,” he corrected.  
  
“Look Sammy, Sam – whatever,” she said slowly. “I’ve got another uh, _appointment_ in one hour, so if we could speed this up.”  
  
“Yeah, I bet you do, probably with sweet lady H,” he said under his breath.  
  
“What was that?” She rasped.  
  
“Uh, nothing. Listen, I just want you to tell me what turns Dean on.”  
  
“I mean, what gets him going? What does he like done to him? That kind of stuff,” He said the shame welling up in his face.  
  
“A lady never tells.” She teased.  
  
“Well, no offence Heather, but you are no lady.”   
  
“You’ve got a lot of balls to say that to me Sammy, I always did like you best.”   
  
“Why do you wanna know anyway? It’s not like you wanna fuck him or anything,” she continued.  
  
Sam looked away, unable to face her eyes.   
  
“Sammy,” She said, lifting his chin and positioning his face so she could see squarely into his eyes.   
  
“I always knew it ya know.”  
  
“I told him, but nobody ever believes crazy old Heather Stevens.”  
  
“What? How did you know?” Sam asked.  
  
“Sam…” She continued. “I’m not blind, even if people were watching you on television they could tell whenever you’re in the same room with Dean the sexual tension is so fucking thick you could cut it with a knife.”  
  
“It’s no wonder people always assume you’re a gay couple.”  
  
“They do not!” he defended.  
  
“Sure they don’t sweetie,” Heather continued, “anyway, when you’re in my line of work you tend not to judge much, so here’s what you have to do.”  
  
Sam listened intently as Heather explained erogenous zones, and how to find Dean’s with little work. She told him about the spot on Dean’s neck that drove him crazy and the one behind his ear.  
  
“Now, when you get down there you really have to use your tongue, he likes that,” she explained, “here, let me draw you a diag—“  
  
“You _don’t_ have to draw me a diagram, but thanks. I think I got it down.”  
  
“Anytime sweetheart,” She said, blowing him a kiss. “Don’t be a stranger,” she said finally, exiting the motel room and disappearing down the hall.  
  
Sam though about some of the things she said. He wasn’t sure if he had the confidence to pull them off, or even if half of them were legal. But, after remembering that look of pleasure Dean had on his face when he fucked Heather he knew she must have done something right.  
  
Dean was going to be making that look a lot after Sam was through, he’d make sure of it.  
  
*****X******  
  
An hour went by before another knock came at the door.  
  
It was a man this time. He was about Dean’s height, and was less bulky but still had some well defined muscles. His hair was blonde and he wore an extremely tight black wife-beater and a pair of jeans.   
  
“Hey, I’m Sam, and you are?” Sam said, outstretching his arm to shake the man’s hand.   
  
“I’m in heaven,” the attractive man said pulling Sam in for a kiss, tracing Sam’s lips with his tongue before shoving it inside.  
  
“Seriously!” Sam yelled. “Can’t I invite a stranger over to a motel for something other than sex?” It took him a moment to realize how stupid that sounded.   
  
“My name’s Kyle, nice to meet you,” the man said, “see? Now we’re not strangers anymore.”  
  
Sam managed to push him off, for a small guy he was actually pretty strong.   
  
“I – I called you over to talk about Dean. Dean Winchester.”  
  
“Dean Winchester?!” The man replied angrily.   
  
“I take it, you know him them.” Sam replied nervously.  
  
The man seemed to hold a deep hatred for Dean, and Sam knew it right away. He knew Dean had been with plenty of men in his lifetime, he just never figured someone like Kyle to be his type. Then again, Kyle was pretty sexy, for a guy and seemed nice enough.  
  
“That arrogant bastard!” Kyle yelled, “is he in here? Where is he?”  
  
“He’s out, I just wanted to ask you a few questions about him.”  
  
“The only thing you need to know about Dean Winchester is that he’s an arrogant son-of-a-bitch who will get up and leave you with no explanation in a moment’s notice.”  
  
“I’m his br—er, I’m his boyfriend,” Sam said, “and really, he’s not like that.”  
  
“Well, last time I saw him he was packing his bags and heading out in that damn car,” Kyle said angrily.  
  
“Why do you hate him so much anyway?” Sam asked, half of him not wanting to know the answer.  
  
“He got into a huge pissy fit, just because I cheated on him 3 times.” Kyle explained.  
  
Did he really just say that? Sam thought. Was this guy really that stupid that he was mad at Dean for leaving him after finding out he had been cheated on 3 times? Sam felt for Dean, deep down Sam knew Dean once cared for this bastard. He also felt a bit relieved knowing Kyle’s tirade about Dean being a total jerk and leaving him for no reason wasn’t true.  
  
“You cheated on him _three_ times?”  
  
“Monogamy is overrated.” Kyle said rather proudly.  
  
“Well, anyway, the reason I called you over here is because I wanna make love to Dean, but, well not _just_ make love to him. I wanna make sure once it’s over he’ll never forget."  
  
“Well, I can help you with that,” Kyle whispered, “Dean may be an arrogant bastard, but he was the best lay I’ve ever had.”  
  
Sam raised an eyebrow rather intrigued. “Really?”  
  
Kyle nodded. “Dean’s a complicated man,” Kyle said, “but making love to Dean Winchester is like riding a bike; once you learn, you  never forget.  
  
Kyle explained how to make Dean bite his lower lip in pleasure, and how to make sure Dean’s cock rubbed against Sam’s prostate.   
  
Armed with the knowledge given to him by the two, Sam guessed he could call them ‘sexperts’, he was pretty sure he could act now. He wanted to be certain Dean would remember this forever, so he decided to make one last phone call to the last person he’d expect himself to call for sex advice.  
  
******X*******  
  
“John Winchester here, whose calling?”  
  
Sam’s stomach lurched, just as he was about to hang up the phone he managed to mumble, “h-hi Dad.”  
  
“What’s the matter Sammy?” John asked. “You’re talking as if you just saw your brother naked or something.”  
  
Somehow, a father always knows Sam thought to himself.  
  
“Listen, I know this is weird and all, but there’s no time to explain.”  
  
“I love Dean, I have for a long time now and I don’t need your judgment but I could really use your help in telling him. I know we’re brothers but look, I just need to know if you’ll help me or not.”  
  
“I see,” John simply replied. “Listen Sam, I’ve known about your little crush on your brother, and honestly, I think he likes you back.”  
  
“How’d you know?” Sam asked shyly.  
  
“Please Sam, a father knows these things. That and the sexual tension is always so—“  
  
“I get it, Dad. How do I tell him?” Sam asked.  
  
“Sam, I know you. Just let your heart finds the words and they will come. I know Dean loves you and all you need to do is tell him.”  
  
Sam smiled a little. That was such a typical ‘Dad’ thing for his father to say.  
  
“And I know you’re thinking that was such a typical Dad thing for me to say, so I’ll just add one more thing. How about showing a little skin every once in a while?”  
  
“You always wear so many layers every damn day and – “  
  
“Thanks Dad,” Sam said smiling before hanging up the phone. His work was done and Dean would be home any minute.  
  
*****X*******  
  
“Hey Sammy,” Dean said closing the motel door and putting the keys to the Impala down on the table.  
  
“Sammy?!” Dean called out. “Where are you?”  
  
“In here!” Sam yelled, hoping his brother would follow his voice into the bedroom.  
  
Dean entered the bedroom and what he saw almost made him faint.  
  
“So Dean, I’ve been talking to some of your old flames and they’ve had some pretty interesting things to say.”   
  
Dean sat down on the bed next to Sam who was only in a pair of silk-satin boxers with hearts printed all over them. Somewhere in the world John Winchester was regretting telling Sam to “show a little skin.”  
  
“Sammy, I –” Dean said before Sam interrupted him, placing his finger on Dean’s lips.   
  
“You don’t have to say anything,” Sam said comfortably.  
  
Sam moved closer to Dean telling him to lift his arms up and he slowly slid his t-shirt off of him.  
  
Sam moved his attention to Dean’s neck, licking and biting the spot on his neck that made Dean groan with delight.   
  
“Sammy, we shouldn’t,” Dean mumbled as Sam continued to assault his face with kisses, making him feel something he had never felt before, true love.  
  
“Shhhh,” Sam said unbuttoning Dean’s jeans and pulling them off his body. He fondled Dean through his boxers and got him hard before pulling them off as well.  
  
Dean gave up resisting. They had gone too far to turn back now, he wanted Sam and nothing would stop him from getting what he wanted.   
  
Sam took Dean’s length into his mouth, tonguing the head and swallowing as much of it as he could. Dean grasped a fistful of Sam’s hair as Sam engulfed him deeper and deeper. Dean always knew Sam lacked a gag reflex, he just could never think of a creative use for it until this point.   
  
His hips began to buck thrusting into Sam’s mouth as Sam’s lips gripped tightly around Dean’s cock.   
  
“I want to feel you inside me,” Sam begged letting go of Dean’s cock getting onto all fours on the bed.  
  
Dean nodded getting on one knee behind Sam and positioning himself at the base of Sam’s ass. He placed his hands on Sam’s shoulders and used them to help him push himself deeper into Sam every time he made a thrust.   
  
Sam winced at the lack of lubrication, the burn almost making him beg for Dean to stop. The pain subsided, becoming more pleasurable as Dean found his prostate, just as Kyle had told him. Dean's cock trailed deeper into Sam's ass, fucking him and making him scream Dean's name out loud. He grasped onto the sheets, squeezing them for dear life as Dean's cock touched his prostate.   
  
Dean's fingers sank into the flesh on Sam's shoulders as he made heavy breaths. He continued to thrust, as his cock moved faster and faster. Dean pulled out all the way, thrusting between Sam's ass cheeks before slamming himself right back in, proving though Sam may have learned a lot, Dean still had a few tricks up his sleeve.  
  
“Wanna see you baby…” Sam mumbled as Dean turned him around, laying him on his back before slamming himself right in. Their bodies touched every time Dean went in for a deep thrust. The muscles around Sam's ass tightened. Holding Dean in place as he began to thrust his hips forward, making Sam scream his name at the top of his lungs.  
  
Sam waited for it, Dean had begun to bite his lower lip. He began to fist himself, the pleasure consuming him. His hand traced his length, as he brought himself closer and closer to orgasm. Dean's cock would not stop grinding it's way inside him and he would have it no other way.  
  
“Sam, baby…” Dean said slowly. Sam just nodded and replied, “I love you.”  
  
In that second Dean spiraled over the edge. He kissed Sam forcefully as he came, unwilling to stop thrusting until his lover had been pushed along with him. He felt Sam's ass tighten around his throbbing cock as he kept pushing, fucking Sam for all he was worth.  
  
Sam felt Dean’s warmth spread inside him, the feeling causing him to come instantly. His come finding itself between their chests.   
  
“I love you too Sammy,” Dean whispered into Sam’s ear, holding him close.  
  
Sam smiled, kissing him.  
  
****X******  
  
The next morning they woke up in each other’s arms, each one of them relieved the events of the previous night had actually transpired.  
  
“Where’d you learn to do all those things Sammy?” Dean questioned, interested to know where Sam learned to have sex like that.  
  
“You wouldn’t believe me even if I told you,” Sam said smiling at him.  
  
******X******  
  
Their bags were packed and they were ready to hit the road again, ready for a new town and new demons to hunt.  
  
Dean had left to start the car and Sam was picking up anything that was left behind in the motel. He went to throw away the gum he’d been chewing when he saw that in the garbage bin was none other than Dean’s little black book.  
  
He smiled getting into the elevator and joining his brother outside in the Impala.  
  
“How come you threw away your book?” Sam asked.  
  
“Somehow Sammy, I don’t think I’m gonna need it anymore.”  



End file.
